


The Prom Dress

by awabubbles



Category: Supernatural
Genre: Crossdressing, First Time, Lace Panties, M/M, Panties, Prom
Language: English
Status: Completed
Published: 2019-05-19
Updated: 2019-05-19
Packaged: 2020-03-08 04:53:39
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,957
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18887557
Author URL: https://archiveofourown.org/users/awabubbles/pseuds/awabubbles
Summary: Dean buys the prom dress Sam has been eyeing for months. They show up as a couple together but never really make it inside.





	The Prom Dress

**Author's Note:**

> Unbeta'd so forgive any errors ❤️

When Sam steps out of the bathroom wearing the dress, Dean’s jaw nearly hits the fucking floor. It’s stunning. Blush-colored satin hugs his brother’s body, tight around the hips and then falling away at the knees. The satin is dark around the mid-section and lighter at the top and bottom for an ombre look, embedded with crystals around the darkest parts. A plunging neckline exposes his perfectly cut pecs and the wide, sleeveless shoulders frame his brother’s T-shaped upper body.

Masculine and feminine, the best of both worlds. Man, Sam wore the shit out of that dress. It gives Dean great pleasure to finally see him in it, makes all those late night shifts at the Super Walmart totally worth it. Dean could have hustled for cash or stolen the dress but he wanted to this the right way. He wanted Sam to feel good about wearing it, no reservations, no excuses. Because Sam deserves the prom dress of his dreams.

Obviously, Dean approves. It’s hard to tell what Sam thinks, though. He’s shy in front of the full length mirror Dean’s set up in their shared bedroom. He keeps turning from side to side, running his fingers over the satin with a neutral expression.

“It makes your tits look great,” Dean offers, a joke that finally puts a smile on Sam’s face, releases the tension in his shoulders.

“Yeah. It’s nice,” Sam finally agrees. “I like it. But I mean...it’s just too bad I can’t wear it.”

Dean’s stomach flips, fists clenching, involuntary. “What do you mean?”

Sam rolls his eyes and scoffs like big brother is so naive. “I can’t show up to prom in a dress! I’ll be the laughingstock of the entire school.” A distant look, his hands exploring the dress again. “But it was nice of you to get it, Dean. Really. I like it alot.”

Sam finally turns and smiles up at him, the expression Dean had been waiting for this whole time but it’s a consolation prize Dean refuses to accept. “If you like it you should wear it,” he insists. “And anybody that even _thinks_ of laughing’ll get my fists in their face!”

Dean widens his stance, squares his shoulders, alpha male on full display. Sam smiles patiently at his big brother. Then he turns back to the mirror, thoughtful.

“Does that mean you’re going to be my date?” Sam asks, eyes downcast.

Dean’s bravado instantly dissolves over his baby brother’s soft voice, pouting lips, slim body contoured in pink satin. He swallows, throat tight. “Guess I could,” he says. “If that’s what you want. But that means you have to wear the dress. Looks good on you, like you were made for it.”

For the past three months Sam has been looking at this dress in the storefront a small shop in Ankeny, Iowa. Dean noticed Sam’s head-turning glances everytime they walked past it, their family headed towards the ammo shop planted beside it instead. Dean had been noticing things like this about his baby brother for awhile now. Sam didn’t like the same toys that defined manhood the way he and John did. Didn’t like leather and grease and the burn of whiskey down your throat. John dismissed it as youthful rebellion but Dean saw something else blossoming. He saw the way Sam lingered in the girls section, touching the fabric, admiring the sequins or the glitter and lace. He saw the way Sam looked at girls his age, hair pulled back, strutting around in short-shorts—not with lust, but envy. All these tiny moments started to paint a bigger picture, something Dean didn’t fully understand yet, but he knew enough to know Sam wanted that dress in the window for his high school prom. So Dean bought it for him. It was as simple as that.

“Okay,” Sam finally agrees. With Dean’s assurance, his confidence returns. Sam looks at himself in the mirror and allows himself to like what he sees. This was him, who he was. “I’ll do it. I'll wear it.”

Sam’s smiles, bright. Dean couldn’t be any prouder.

~~~~

One week later they go to Sam’s highschool prom together. Dean pulls up in the school’s parking lot wearing his father’s leather jacket, like he always does, but this time he’s jazze it up a bit with a white button down shirt, and a clip-on tie. In the backseat, Sam is in the dress. He’s dolled up with some glitter on his lips, heels on his feet, and a corsage to match the one pinned to Dean’s shirt. He’s fucking gorgeous. Honestly Dean’s never seen anyone as pretty as his baby brother tonight. Everytime he looks at Sam he gets butterflies in his stomach.

“We’re here,” Dean announces, pulling the keys out of the ignition. “Hang on and I’ll get the door for you, princess.”

He jumps out to hold open the driver’s side back door, offering a gentlemanly hand to assist Sam out of the car. But his brother doesn't take it. Instead, he remains seated, staring at his own hands curled into his lace-clad lap.

Dean’s stomach sinks. Was Sam having second thoughts?  “You comin’,” he asks.

Sam glances up, smiling sadly. He scoots over to the other side of the car and pats the seat, an invitation to talk. Hesitant, Dean slides into the backseat next to Sam and closes the door.

“I know you did this all for me so I don’t want you to be dissapointed,” Sam says. “But I only came out tonight to prove something to myself. And now that I’m here, I think...this is enough. Just this. Right here.”

Dean shifts on the vinyl seats. He’s not dumb. He knows someone that looks like Sam, in a dress, will get a lot of looks. He knows it takes a hell of a lot of guts for Sam to get this far. But Dean also knows it’s his job to support his brother and not to push him to do something he’s not comfortable with. “I thought this is what you wanted.”

“I wanted to be who I really am with someone who understands me,” Sam says, smiling shyly at his big brother. “I already got that so going out there with all those other kids—I don’t know. I don’t care what they think. I don’t have anything to prove to them.”

Dean half-smiles, disappointed but pleased all at once. “Too bad,” he teases. “I wanted everybody to see me making out with the hottest girl at the party.”

Sam bats his lashes and smirks. “You can still do that.”

The suggestion sends a jolt between Dean’s spread thighs. Parted lips, half-lidded eyes, like the invitation to sit beside him in the car, only this time Dean doesn’t hesitate. He leans in to kiss his baby brother’s glitter-glossed lips. Puckered, soft, and sweet like candy, they ignite something in Dean’s belly. A chaste little peck becomes something deeper, hungrier, until Dean’s tongue is lapping at his baby brother’s moans, hands sliding up under the slit in Sam’s skirt.

While Dean has been noticing Sammy’s drift towards the feminine, he’s also just been _noticing_ Sammy. Noticing the pout in his brother’s lips, the flush in his cheeks, the swing of his hips, the length of his mile-long legs. And Sam has been noticing him noticing as well. He bathes in Dean’s attention, arching his neck, fluttering his lashes, or just plain sticking out his ass for his big brother to admire. It’s been a strange kind of game between them for a few years now. Unspoken, under the surface; just like the dress. And now that Sam has embraced this part of himself, well, Dean can hardly resist from embracing Sam as well.

So Dean kisses his baby brother in the backseat of their dad’s Chevy Impala until it makes him dizzy with desire. He can’t get enough of Sam’s little sighs as his hand slips up under Sam’s satin dress and in between his smooth pale thighs. Like a good little boy Sam spreads his legs and that’s when Dean’s greedy fingers find the lacey sheen of fabric cupping his brother’s half-hard cock.

“What the fuck?” Dean whispers into Sammy’s flush-red lips. He drags his thumb over Sam’s dick again to confirm. Yes. Lace. Under the satin dress Sammy was wearing a pair of tight lace panties.

“I had to wear something just as nice, underneath,” Sammy purrs. Hitching his skirt up he shows Dean the white lace panties delicately hugging the curve of his hips and the bulge of his cock. A tiny pink garter belt stretches across the lace, clipping onto Sam’s white lace-trimmed stockings.

It’s the hottest thing Dean’s ever fucking seen. He nearly busts a nut right then and there. “Holy shit, Sammy,” he breathes. “You were wearing these under there....this whole time?”

Sam bites his lip, nods. “I wanted to feel pretty.”

“So pretty,” Dean agrees. Dropping his head between Sam’s spread thighs he leaves a trail of kisses down to Sam’s cock. “So. Fucking. Beautiful.” When Dean reaches Sam’s naughty secret he presses a kiss to the tip of Sam’s lace-clad dick and is rewarded with a trembling sigh from his baby brother. Again. Again, and this time and this time Dean drags tongue across the lace, nipping playfully and the fabric but also lapping and sucking at the cock beneath.

“Aaaahhh. Fuck!” his baby brother moans, grabbing fistfuls of his hair.

Delicious. Dean is already fucking addicted. Lick-suck-slurp—Dean eats Sammy out like there really is a pair of pink pussy lips beneath the lace, in love with every desperate moan and wanton sigh that trickles into his ear.

It’s a short stay in paradise, though, Sam’s virginal cock doesn’t last long at his attention. There’s a “Mmmm—my—god!” and then Sam throws back his head back and explodes inside his lacy white cage. Dean watches with great delight as a tiny dark stain spreads until Sam’s panties are completely jizz-soaked.

“Think you ruined your lace there, baby boy,” Dean muses. “Gonna have to take ‘em off so they don’t ruin that dress.”

With nothing but a whimper-moan protest from Sam, Dean hooks his fingers into the top of Sam’s panties and garter belt and slowly pulls them down. He drinks in the sight of Sam’s hipbones, his neatly cut pubes, his pink-flushed cock lazily draped across his stomach. Dean rolls the panties down the rest of Sam’s legs, slips it past his heels and drops the soaking bundle onto the floor of the Impala with a salacious _squelch_. But there’s still jizz left on Sammy’s cock. Like a good big brother he laps the rest of it up, but Sam is sensitive after coming and he squirms under Dean’s attention.

“Hnnngh. Wait. Dean.”

Dean relents. He releases his brother’s cock,  sits back on his heels. He realizes then just how hard and desperate his own cock is for attention. “Sam,” he warns. “I gotta—”

“Not the dress,” Sam reminds, voice breathy and sex-drenched. “You don’t want to ruin in remember?”

Dean is about to argue but then Sam lifts his right leg and shows Dean his tight pink little hole, soft and satiny just like the dress Sam’s wearing. “Come in here, instead,” he says.

Dean’s lust is a strangled groan. Parting Sam’s soft fleshy cheeks Dean admires the quivering, virgin hole before him. Fuck, he’s dreamed about this, wet dreams rudely awakened by the reality that Sam was his brother—and therefore, off limits. But something was different about tonight. Sam was defying everyone in his pink satin dress, and together, they defied something else entirely. His baby brother probably had words for all of this: gender, societal taboos. But all Dean cared about was how right this felt. That, and how fucking hot Sam looked: dress hiked up, panties shed, red heels pointed, and legs spread waiting for his big brother to use him. Yeah. Dean was going to use the fuck out of him alright.

Dean dives back in between his baby’s brothers legs with renewed vigor. He suck-licks Sammy’s pretty pink hole until it gapes just wide enough to wriggle a tongue inside of him. Dean laps Sammy’s insides, nose crammed into Sam’s stretched taint as Dean pushes his tongue in as deep it'll go. His baby brother’s ass tastes good, fuck, but Dean’s cock is so hard he feels fucking dizzy from want. He pushes a finger inside Sam’s tight virgin ass. It shivers, resists, but then finally allows Dean’s single, solitary finger inside.

Jesus. This was going to take forever.

“My clutch,” Sam whimpers, gesturing at the floor.

Beside Sam’s jizz-soaked panties is a sequined clutch with a clasp top. Dean opens it up to find a bottle of lube inside. He’s at once appalled and excited at how prepared Sam is for tonight. Opening the lube, Dean slathers his fingers in Astroglide and immediately slides two of them inside. Sam gasps, clenches around Dean, but after a little coaxing he starts to relax. Dean fingers his brother, feels him opening it up. Quickly, Dean takes his free hand and undoes his jeans. Grabbing his own cock, he strokes it like a come-starved man.

“You’re so fucking beautiful,” Dean pants. “I can’t believe your mine, Sammy.”

Sam smiles, hair hanging in his face, lashes fluttering against his cheeks. “Not yet. You still have to make me yours,” he says.

Dean groans. He can’t hold back any longer. He pulls his lube-slicked fingers out of his baby brother’s ass and with both hands pushes his pants down past his hips. Sam lays back on Impala’s vinyl seats, satin dress spread out behind. Dean kneels between his baby brother’s spread legs and positions his cock against Sam’s hole.

“This might hurt,” he warns.

Sam just nods, glitter spread sloppily over his puffy red lips. “I want it to,” he says. “That’s how I know it’s real.”

Dean shudders, kisses his brother hungrily, and then pushes his cock inside.

“Hnnggh. Fuck,” Sam whines.

It's tight, but Dean keeps pushing until the head of his cock is past that thick ring of muscle, then the rest of him slides in a little easier. Once he’s inside, Dean lets his little brother adjust.

“This is more of a prom night tradition then corsages and slow dances isn’t it?” Dean asks with a dark chuckle. “Losing your virginity in the backseat of a car. You and all the dirty girls at your school finally have something in common, Sammy.”

Sam wraps his legs around Dean, heels clicking as his ankles overlap. “Except they don’t get you,” he says, fingers trailing like fire over the back of Dean’s neck. “Only I get you, big brother. All to myself.”

Dean falls into another heated kiss with Sam, hands twined into each other’s hair; joined at the lips, and the hips. Intoxicated, Dean moves starts to fuck him oh-so-gently. Sam reciprocates with a gentle moan, his wrung-out cock filling up again as Dean starts to move inside of him. Knowing Sam feels as good as he does Dean pulls out a little farther, pushes his cock in a little deeper. He relishes the feel of Sam’s tightly clenched hole as he drags his cock out of Sam’s ass, relishes the enveloping warmth as he pushes it back inside his brother’s welcoming body.

They fuck on the backseat of their dad’s Chevy Impala, bathed in the soft glow of parking lot lights as the highschool’s prom goes on without them. Buried inside of his own brother, Sam and Dean create a lovestory amongst themselves: the two of them against the world, just like it’s always been. Dean fucks Sam in a pink satin dress with heels stacked against his back and he could give a fuck what the world thinks. The only thing that’s ever mattered to him was Sammy, now beneath him, wrapped tightly around his cock, moaning his name.

“I’m gonna come,” Dean pants. As much as he wants this to last forever, his body has already been on edge for too long. “I’m gonna inside of you baby boy. Fuck, I’m gonna get you pregnant on your first time.”

“Shit,” Sammy shudders, jacking his own cock in time to his brother’s thrusts. “Do it. Come inside. I want you to fill me up.”

Dean doesn’t need more incentive. With permission, he comes, his orgasm ripping like a tidal wave across his body. Dean groans, practically goes blind with pleasure as he finally explodes inside of his baby brother’s shivering hole. Sam feels Dean’s warmth flooding his insides. Throwing his head back, Sam comes for a second time, shooting hot streams of come across his stomach, and even, horrifyingly, onto his own dress.

Neither of them realize the mistake until several minutes later, when it’s already started to dry on the ombre satin. By then, Dean has pulled out and his come has started to spill out of his baby brother, staining the dress in a second spot. Sam fingers his fucked-open hole with reverence, Dean’s come still gushing out of him.

They look at each other and laugh.

“So much for your prom dress, Sammy,” Dean says. “It lasted you all of one night.”

Sam smiles mischievously, cheeks fuck-flushed and lips lecherously red. “That’s okay,” he forgives. “You can buy me another dress to fuck me in."

Dean huffs but his just-spent cock twitches with renewed interest. “Wouldn’t a new pair of panties be cheaper?”

“Both are good,” Sam concludes. Before Dean can protest, Sam draws him into another long kiss. They fall back together onto Impala’s backseat, permanently entwined, for the rest of their lives.


End file.
